CA2754831A1 - Novel sodium channel blocking compounds tetrodotoxin galactopyranosides - Google Patents
Novel sodium channel blocking compounds tetrodotoxin galactopyranosides Download PDFInfo
- Publication number
- CA2754831A1 CA2754831A1 CA2754831A CA2754831A CA2754831A1 CA 2754831 A1 CA2754831 A1 CA 2754831A1 CA 2754831 A CA2754831 A CA 2754831A CA 2754831 A CA2754831 A CA 2754831A CA 2754831 A1 CA2754831 A1 CA 2754831A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- galactoside
- isolated
- tetrodotoxin
- pain
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Novel sodium channel blocking compounds tetrodotoxm galactopyranosides of formula I were isolated and puri-fied by HPLC and identified further through IR, NMR, GC, and MS. The compounds have a galactopyranosyl moiety attached to C11 of tetrodotoxin and retain the analgesic activity of the latter.
Pharmaceutical compositions and medical uses thereof are further disclosed.
Pharmaceutical compositions and medical uses thereof are further disclosed.
Claims (13)
1. An isolated or purified compound of Formula I, or the pharmaceutically acceptable salt, solvate, or hydrate, form thereof, wherein the substituent at C-11 is a galactoside.
2. The compound of claim 1, wherein the isomeric form of the galactoside of said compound is D-galactoside.
3. The compound of claim 1, wherein the isomeric form of the galactoside of said compound is L-galactoside.
4. The compound of any one of claims 1 to 3, wherein said compound has been isolated from a species selected from the group consisting of puffer fish, goby fish, newt, frogs, blue ringed octopus and marine algae.
5. The compound of any one of claims 1 to 4, wherein said compound is isolated from puffer fish.
6. The compound of any one of claims 1 to 3, wherein said compound is purified from a preparation of tetrodotoxin (TTX), wherein said TTX has been isolated from a species selected from the group consisting of puffer fish, goby fish, newt, frogs, blue ringed octopus and marine algae.
7. The compound of any one of claims 1 to 6, wherein said compound is greater than 70%
pure.
pure.
8. The compound of any one of claims 1 to 6, wherein said compound is greater than 90% pure.
9. A pharmaceutical composition comprising the compound of any one of claims 1 to 8, further admixed with one or more pharmaceutically acceptable excipient(s).
10. A method for treating pain, comprising administering a therapeutically effective amount of a compound of any one of claims 1 to 9 to a subject in need thereof.
11. The method of claim 10, wherein said pain is neuropathic pain, visceral pain or somatic pain.
12. The method of claims 10 or 11, wherein said administration is systemic administration.
13. The method of claim 12, wherein said systemic administration is performed by intramuscular injection, subcutaneous injection, or intravenous injection.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21147109P | 2009-03-30 | 2009-03-30 | |
| US61/211,471 | 2009-03-30 | ||
| PCT/CA2010/000470 WO2010111777A1 (en) | 2009-03-30 | 2010-03-26 | Novel sodium channel blocking compounds tetrodotoxin galactopyranosides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2754831A1 true CA2754831A1 (en) | 2010-10-07 |
Family
ID=42827439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2754831A Abandoned CA2754831A1 (en) | 2009-03-30 | 2010-03-26 | Novel sodium channel blocking compounds tetrodotoxin galactopyranosides |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8486901B2 (en) |
| EP (1) | EP2414373A4 (en) |
| CN (1) | CN102439022A (en) |
| AU (1) | AU2010230805A1 (en) |
| CA (1) | CA2754831A1 (en) |
| WO (1) | WO2010111777A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2638908A1 (en) * | 2012-03-16 | 2013-09-18 | Phytotox SpA | Paralytic Shellfish Poison |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1240702C (en) * | 2000-09-18 | 2006-02-08 | 威克斯医药有限公司 | Process for extracting tetrodosin with high output rate |
| CN1187355C (en) * | 2000-11-22 | 2005-02-02 | 南宁枫叶药业有限公司 | Method for refining high-purity tetradoxin |
| EP1931349A4 (en) * | 2005-08-25 | 2009-08-05 | Wex Pharmaceuticals Inc | Use of sodium channel blockers for the management of musculoskeletal pain |
-
2010
- 2010-03-26 WO PCT/CA2010/000470 patent/WO2010111777A1/en active Application Filing
- 2010-03-26 CA CA2754831A patent/CA2754831A1/en not_active Abandoned
- 2010-03-26 US US13/258,529 patent/US8486901B2/en active Active
- 2010-03-26 AU AU2010230805A patent/AU2010230805A1/en not_active Abandoned
- 2010-03-26 EP EP10757967A patent/EP2414373A4/en not_active Withdrawn
- 2010-03-26 CN CN2010800151459A patent/CN102439022A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP2414373A4 (en) | 2013-01-02 |
| US20120101054A1 (en) | 2012-04-26 |
| EP2414373A1 (en) | 2012-02-08 |
| CN102439022A (en) | 2012-05-02 |
| WO2010111777A8 (en) | 2012-03-29 |
| WO2010111777A1 (en) | 2010-10-07 |
| US8486901B2 (en) | 2013-07-16 |
| AU2010230805A1 (en) | 2011-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |
Effective date: 20140326 |